1. Field of the Invention
This invention describes polyols which are useful, among other purposes, in the manufacture of urethane polymers.
2. Description of the Art Practices
It is known that polyols may be formulated from many materials. For instance the work of Hostettler, and Hostettler et al. in U.S. Pat. No. 2,933,477 issued Apr. 19, 1960; U.S. Pat. No. 2,962,524 issued Nov. 29, 1960; and U.S. Pat. No. 2,962,455 issued Nov. 29, 1960, teaches that caprolactone may be utilized to form polyols which are then useful in the formation of other materials such as urethanes. However, the Hostettler, and Hostettler et al materials are solids and thus are of limited utility because they must be heated above their melting point in order to be capable of reacting effectively with other materials.
It is known from U.S. Pat. No. 2,599,468 issued June 3, 1952 to McKeever that 9(10)hydroxymethyloctadecanol may be prepared. This material is normally a solid although it is sometimes found as a super cooled liquid. While this material might be useful for several purposes it is expensive to obtain in that the normal route of processing is from oleic acid. That is, while the hydroxymethyl formation through the oxo process may be conducted relatively simply on this material, there is difficulty and expense involved in converting the carboxylic group to an alcohol. DeWitt et al. in U.S. Pat. No. 3,242,414 issued Mar. 29, 1966 discloses that electrically resistant materials may be formed from the alcohols described in the aforementioned McKeever patent. It is known that acrylic esters of the materials of McKeever may be formulated through the disclosures of Offenlegungsschrift No. 2,200,021 published July 26, 1973 by Wegemund. It is also known from U.S. Pat. No. 3,043,871 to Buchner et al. issued July 10, 1962 that the diacid corresponding to the alcohol of McKeever may be formed.
The work of the United States Department of Agriculture at the Northern Regional Laboratory at Peoria, Ill., has lead to the conversion number of unsaturated fatty compounds which may be further converted to useful materials. For instance, in U.S. Pat. No. 3,787,459 issued Jan. 22, 1974 to Frankel there is disclosed formyl derivatives of carboxylic acids. In U.S. Pat. No. 3,928,231 issued Dec. 23, 1975 to Frankel there is also disclosed the formation of polycarboxylic acids derived from fatty materials. In U.S. Pat. No. 4,093,637 issued June 6, 1978 to Miller the use of esters of fatty derived materials as polyvinylchloride plasticizers is disclosed. Esters of materials containing hydroxyl groups are described in U.S. Pat. No. 4,083,816 issued Apr. 11, 1978 to Frankel et al.
There are further disclosures of materials by the United States Department of Agriculture in a paper entitled Carboxystearic Acid Esterification and Interchanges dated Nov. 11, 1971 by Dufek et al. A second publication of Dufek et al entitled Some Esters of Mono- Di- and Tricarboxystearic Acid as Plasticizers; Preparation and Evaluation, Volume 53 JAOCS, p. 198, May 1976 discusses the uses of polycarboxylate esters. The formation of a hydroxymethyl triglyceride product of hydroformylation and hydrogenation of oleic safflower oil is referred to by Frankel et al in JAOCS Vol. 48, No. 5, p. 248 entitled Methyl 9(10)-Formylstearate by Selective Hydroformylation of Oleic Oils. Hydroxymethyl fatty alcohols are also described in the work of Frankel et al in JAOCS Vol. 52, 12, p. 498, 1975, entitled Acyl Esters of Oxo-Derived Hydroxymethylstearates as Plasticizers for Polyvinyl Chloride.
It is also known from German Pat. No. 934889 published Nov. 10, 1955 that certain tricyclic esters may be formed. Similar work in this regard is found in U.S. patent application Ser. No. 194,172 by Rogier filed Oct. 6, 1980. Similar disclosures of polycyclic alcohols are found in Offenlegungsschrift No. 2,200,022 laid open for inspection July 19, 1973. Further disclosures of such materials are found in derivatives of Dicyclopentadiene-Valuable Key Compounds, Cornils et al published in Chemiker Zeitung 98, (2), 70-76, 1974.
The disclosures of the foregoing references, to the extent that they are applicable to the present invention, are hereby incorporated by reference.